Resolution of isoborneol and its isomers by GC/MS to identify "synthetic" and "semi-synthetic" borneol products

Chirality
Ming-Yeh YangTzenge-Lien Shih

Abstract

Borneol is a plant terpene commonly used in traditional Chinese medicine. Optically pure (+)-borneol and (-)-borneol can be obtained by extraction from the plants Dipterocarpaceae and Blumea balsamifera, respectively. "Synthetic borneol" is obtained from the reduction of (±)-camphor to lead to four different stereoisomers: (+)-isoborneol, (-)-isoborneol, (+)-borneol, and (-)-borneol. In contrast, "semi-synthetic borneol" is produced from the reduction of natural camphor, (+)-camphor, to afford two isomers: (-)-isoborneol and (+)-borneol. We established a convenient method to identify them by treating the four stereoisomers with two chiral reagents, (R)-(+)-α-methoxy-α-trifluoromethylphenylacetyl chloride ((R)-(+)-MTPA-Cl) and (1S)-(-)- camphanic chloride. The resulting derivatives from the above mentioned method were analyzed by gas chromatography. The enantiomers of (+)- and (-)-isoborneol were successfully separated from (+)- and (-)-borneol isomers in this study to make this a useful method in the identification of "synthetic" and "semi-synthetic" borneols. Furthermore, we also examined five different commercial borneols. During this course, a novel and unprecedented partial epimerization from isoborneol-camphanic ester to b...Continue Reading

References

Dec 14, 2004·European Journal of Pharmacology·Adam C HallLâle A Burk
May 16, 2014·Journal of Asian Natural Products Research·Hai-Li XinGuan-Jun Wang
Feb 2, 2018·Journal of Food and Drug Analysis·Tsung-Jung HoHao-Ping Chen

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Citations

Apr 24, 2021·Pharmacological Research : the Official Journal of the Italian Pharmacological Society·Songyu LiuJunzhi Lin
May 26, 2021·Chembiochem : a European Journal of Chemical Biology·Elia CalderiniRobert Kourist

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